Benzenesulphonylbenzenesulphonamideazophenyl-or-naphthyl-azolhydroxyloweralkoxyphenyl dyestuffs

ABSTRACT

Dyestuffs of the formula ##STR1## wherein B represents a 1,4-phenylene, 5,6,7,8-tetrahydro-1,4-naphthylene or 1,4-naphthylene radical, 
     R 1  represents an aromatic, aliphatic or dialkylamino radical, 
     R 2  represents chlorine, bromine, an alkyl group or an alkoxy group, 
     R 3  and R 4  represent hydrogen, chlorine, bromine, an alkoxy group or an alkyl group, 
     R 5  and R 6  represent hydrogen, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms, 
     R 7  represents ##STR2## R 8  and R 10  represent hydrogen or methyl, R 9  represents methyl, ethyl, phenyl, hydroxymethyl, C 1  -C 4  -alkoxymethyl, benzyloxymethyl, C 1  -C 4  -alkylcarbonyloxymethyl or C 2  -C 4  -alkenylcarbonyloxymethyl, the radical OR 7  is in the o- or p-position relative to the azo bridge, and 
     m represents a number from 0 to 2, 
     Are suitable for dyeing and printing natural and synthetic fibre materials containing amide groups.

The subject of the present invention are new, valuable disazo dyestuffs which in the form of the free acid correspond to the general formula ##STR3## and their preparation and use for dyeing synthetic fibre materials, especially those consisting of polyamides.

In the general formula (I),

R₁ represents an aromatic, aliphatic or dialkylamino radical,

R₂ represents chlorine, bromine, an alkoxy group or an alkyl group,

R₃ and R₄ represent hydrogen, chlorine, bromine, an alkoxy group or an alkyl group,

R₅ and R₆ represent hydrogen, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms,

R₇ represents ##STR4## R₈ and R₁₀ represent hydrogen or methyl, R₉ represents methyl, ethyl, phenyl, hydroxymethyl, C₁ -C₄ -alkoxymethyl, benzyloxymethyl, C₁ -C₄ -alkylcarbonyloxymethyl or C₂ -C₄ -alkenylcarbonyloxymethyl, B represents a 1,4-phenylene, 1,4-naphthylene or 5,6,7,8-tetrahydro-1,4-naphthylene radical and

m represents a number from 0 to 2.

Examples of suitable radicals B are radicals of the formulae ##STR5## wherein R₃ and R₄ have the abovementioned meaning.

Preferred alkyl groups are those with 1-4 C atoms. The alkyl and alkoxy groups can be substituted further, for example by halogen, nitrile, hydroxyl or optionally substituted phenyl. Examples of suitable alkyl groups are --CH₃, --C₂ H₅, --C₃ H₇, --C₄ H₉, --C₂ H₄ CN, --CH₂ --C₆ H₅ and CF₃.

Preferred alkoxy groups are those with 1-4 C atoms. Examples of suitable alkoxy groups are --OCH₃, --OC₂ H₅, --OC₃ H₇, --OC₄ H₉, --OCH₂ CH₂ OH and --OCH₂ C₆ H₅.

Examples of suitable aromatic radicals R₁ are optionally substituted phenyl radicals; examples of suitable aliphatic radicals are C₁ -C₄ -alkyl radicals; the dialkylamino groups in particular contain C₁ -C₄ -alkyl groups. Preferably, R₁ represents phenyl optionally substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, nitrile or nitro, or represents C₁ -C₄ -alkyl, but in particular phenyl and methylphenyl.

The disulphimide group of the formula (I) is in the ortho-, meta- or para-position relative to the azo bridge and the radical OR₇ is in the ortho- or para-position relative to the azo bridge.

Preferred dyestuffs are those of the formula ##STR6## wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇ and m have the above-mentioned meaning,

as well as those of the formula ##STR7## wherein R₁, R₂, R₅, R₆, R₇ and m have the abovementioned meaning.

Further preferred dyestuffs are those of the formula ##STR8## wherein R₁, R₂, R₅, R₆, R₇ and m have the abovementioned meaning.

Particularly valuable dyestuffs are those of the formula ##STR9## wherein R₁, R₂, R₃, R₄, R₅, R₆ and R₇ have the abovementioned meaning and

m' represents 0 or 1,

especially those of the formula ##STR10## wherein R₂, R₃, R₄, R₅ and R₆ have the abovementioned meaning and

R₁ ' represents an optionally substituted phenyl radical,

R₇ ' represents 2-hydroxypropyl or 2-hydroxybutyl and m' represents 0 or 1.

Further particularly valuable dyestuffs are those of the formula ##STR11## wherein R₁, R₂, R₅, R₆ and R₇ have the abovementioned meaning and

m' represents 0 or 1,

especially those of the formula ##STR12## wherein R₂, R₅ and R₆ have the abovementioned meaning and

R₁ ' represents an optionally substituted phenyl radical,

R₇ ' represents 2-hydroxypropyl or 2-hydroxybutyl and

m' represents 0 or 1.

Further preferred dyestuffs correspond in the free acid form to the formula ##STR13## wherein R₁ ' represents an aromatic radical or an aliphatic radical with 1-4 carbon atoms,

R₂ ' represents hydrogen, chlorine, bromine, a methoxy or ethoxy group, a methyl or ethyl group or a trifluoromethyl group,

R₃ ' represents hydrogen, chlorine, a methyl or methoxy group or an ethyl or ethoxy group,

R₄ ' represents hydrogen, a methyl or methoxy group or an ethyl or ethoxy group,

R₅ ' and R₆ ' independently of one another represent hydrogen, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms, and

R₇ ' represents 2-hydroxypropyl or 2-hydroxybutyl.

and the formula ##STR14## wherein R₁ " represents an optionally substituted phenyl radical,

R₂ " represents hydrogen, chlorine, bromine, a methoxy or ethoxy group, a methyl or ethyl group or a trifluoromethyl group,

R₃ " represents hydrogen, chlorine, a methyl or methoxy group or an ethyl or ethoxy group,

R₄ " represents hydrogen, a methyl or methoxy group or an ethyl or ethoxy group,

R₅ " and R₆ " independently of one another represent hydrogen, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms, and

R₇ ' represents 2-hydroxypropyl or 2-hydroxybutyl.

Other valuable dyestuffs are in the free acid form of the formula ##STR15## wherein B' represents a 1,4-naphthylene radical or a 5,6,7,8-tetrahydro-1,4-naphthylene radical,

R₁ represents an aromatic radical or an aliphatic radical with 1-4 C atoms,

R₂ represents chlorine, bromine, an alkoxy group or an alkyl group,

R₅ and R₆ independently of one another represent hydrogen, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms,

R₇ represents ##STR16## R₈ and R₁₀ represent hydrogen or methyl, R₉ represents methyl, ethyl, phenyl, hydroxymethyl, C₁ -C₄ -alkoxymethyl, benzyloxymethyl, C₁ -C₄ -alkylcarbonyloxymethyl or C₂ -C₄ -alkenylcarboxyloxymethyl, and

m represents a number from 0 to 2;

of the formula ##STR17## wherein B' represents a 1,4-naphthylene radical or a 5,6,7,8-tetrahydro-1,4-naphthylene radical,

R₁ ' represents an aromatic radical or an aliphatic radical with 1-4 C atoms,

R₂ ' represents hydrogen, chlorine, bromine, a methoxy or ethoxy group, a methyl or ethyl group or a trifluoromethyl group,

R₅ ' and R₆ ' independently of one another represent hydrogen, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms, and

R₇ ' represents 2-hydroxypropyl or 2-hydroxybutyl.

and of the formula ##STR18## wherein B' represents a 1,4-naphthylene radical of a 5,6,7,8-tetrahydro-1,4-naphthylene radical,

R₁ " represents an optionally substituted phenyl radical,

R₂ " represents hydrogen, chlorine, bromine, a methoxy or ethoxy group, a methyl or ethyl group or a trifluoromethyl group,

R₅ " and R₆ " independently of one another represent hydrogen, an alkyl group with 1-4 C atoms or an alkoxy group with 1-4 C atoms, and

R₇ ' represents 2-hydroxypropyl or 2-hydroxybutyl.

The dyestuffs of the formula (I) are prepared in a known manner by diazotising amines of the formula ##STR19## wherein R₁, R₂ and m have the abovementioned meaning and reacting the products with amines of the formula ##STR20## wherein R₃, R₄ and B have the abovementioned meaning and

Z represents H, --SO₃ H or --CH₂ SO₃ H

to give monoazo dyestuffs of the formula ##STR21## diazotising the monoazo dyestuffs thus obtained, if necessary after splitting off the group Z by alkaline or acid saponification, coupling the product with phenols which couple in the ortho- or para-position to the OH group, of the formula ##STR22## wherein R₅ and R₆ have the abovementioned meaning, and then alkylating the disazo dyestuffs of the formula ##STR23## with appropriate alkylene oxides of the formula ##STR24##

Suitable disulphimides of the formula (IX) are for example: (3-amino-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-benzenesulphonamide, (3-amino-benzenesulphonyl)-methanesulphonamide, (3-amino-benzenesulphonyl)-propanesulphonamide, (3-amino-benzenesulphonyl)-butanesulphonamide, (3-amino-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-methanesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-butanesulphonamide, (3-amino-4-chloro-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-butanesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-methanesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-methyl-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-methyl-benzenesulphonyl)-methanesulphonamide, (3-amino-4-methoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-methoxy-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-methoxy-benzenesulphonyl)-methanesulphonamide, (3-amino-4-methoxy-benzenesulphonyl)-butanesulphonamide, (3-amino-6-methoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-methoxy-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-methoxy-benzenesulphonyl)-methanesulphonamide, (3-amino-6-methoxy-benzenesulphonyl)-butanesulphonamide, (2-amino-benzenesulphonyl)-benzenesulphonamide, (2-amino-benzenesulphonyl)-p-toluenesulphonamide, (2-amino-benzenesulphonyl)-o-toluenesulphonamide, (2-amino-benzenesulphonyl)-methanesulphonamide, (2-amino-benzenesulphonyl)-butanesulphonamide, (3-amino-6-ethyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-ethyl-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-ethyl-benzenesulphonyl)-methanesulphonamide, (3-amino-4-ethyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-ethoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-ethoxy-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-chloro-benzenesulphonyl)-benzenesulphonamide, (3-amino-6-chloro-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-6-chloro-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-benzenesulphonyl)-methanesulphonamide, (4-amino-benzenesulphonyl)-butanesulphonamide, (3-amino-4-bromo-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-bromo-benzenesulphonyl)-p-toluenesulphonamide, (3-amino-4-bromo-benzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-bromo-benzenesulphonyl)-methanesulphonamide, (3-amino-4-bromo-benzenesulphonyl)-butanesulphonamide, (2-amino-3-chloro-4-methyl-benzenesulphonyl)-benzenesulphonamide, (2-amino-3-chloro-4-methoxy-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-chloro-5-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-5-chloro-6-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-5-chloro-6-methyl-benzenesulphonyl)-methanesulphonamide, (4-amino-5-chloro-benzenesulphonyl)-benzenesulphonamide, (4-amino-3-chloro-benzenesulphonyl)-methanesulphonamide, (4-amino-5-methyl-benzenesulphonyl)-methanesulphonamide, (4-amino-5-methyl-benzenesulphonyl)-benzenesulphonamide, (3-amino-4-trifluoromethyl-benzenesulphonyl)-benzenesulphonamide, (4-amino-3-trifluoromethyl-benzenesulphonyl)-methanesulphonamide, (3-amino-benzenesulphonyl)-dimethylsulphamic acid amide and (3-amino-benzenesulphonyl)-dibutylsulphamic acid amide.

Examples of suitable middle components of the formula (X) are: aniline, 2-aminotoluene, 3-aminotoluene, 2-amino-ethylbenzene, 3-amino-ethylbenzene, 3-chloroaniline, 3-bromo-aniline, 2-aminoanisole, 3-aminoanisole, 2-amino-ethoxybenzene, 3-amino-ethoxybenzene, 1-amino-2,3-dimethylbenzene, 1-amino-2,5-dimethylbenzene, 1-amino-3,5-dimethylbenzene, 3-amino-4-methoxy-toluene, 2-amino-4-methoxy-toluene, 2-amino-1,4-dimethoxy-benzene, 2-amino-4-ethoxy-toluene, 2-amino-1,4-diethoxy-benzene, α-naphthylamine, 5,6,7,8-tetrahydro-1-naphthylamine and their N-sulphonic acids or their N-ω-methanesulphonic acids.

The following may be mentioned as examples of suitable end components of the formula (XII): phenol, o-cresol, m-cresol, p-cresol, 1-hydroxy-4-ethyl-benzene, 1-hydroxy-4-tertiary butyl-benzene, 1-hydroxy-2-ethyl-benzene, 1-hydroxy-2-isopropyl-benzene, 1-hydroxy-2-secondary butyl-benzene, 3-hydroxy-1,2-dimethyl-benzene, 2-hydroxy-1,4-dimethyl-benzene, 4-hydroxy-1,2-dimethyl-benzene, 2-hydroxy-1,3-diethyl-benzene, 1-hydroxy-2-methoxy-benzene, 1-hydroxy-3-methoxy-benzene, 1-hydroxy-3-ethoxy-benzene, 1-hydroxy-4-butoxy-benzene and 1-hydroxy-3-butoxy-benzene.

Examples of suitable alkylene oxides are propylene oxide, 1,2- and 2,3-butylene oxide, styrene oxide, glycidol, glycidyl methyl ether, glycidyl acetate, glycidyl propionate, glycidyl methacrylate, glycidyl benzyl ether and isobutylene oxide.

The diazotisation of the amines of the formula (IX) is carried out according to methods which are in themselves known, preferably with sodium nitrite in aqueous solution containing mineral acid. The coupling of the diazonium compounds of the amines of the formula (IX) with the coupling components of the formula (X) can be carried out in accordance with processes which are in themselves known, for example in a neutral to strongly acid, but preferably in a weakly acid, pH range, in an aqueous or aqueous-organic medium.

The monoazo dyestuffs of the formula (XI) are isolated in accordance with known methods, for example by filtration or by salting out with a salt soluble in aqueous solution, for example with NaCl or KCl, followed by filtration. If coupling components of the formula (X) with Z = SO₃ H or --CH₂ --SO₃ H are employed, isolation of the monoazo dyestuffs is frequently only necessary after the amino group of the coupling component has been liberated by alkaline or acid saponification. However, an intermediate isolation of the monoazo dyestuffs is not always necessary - they can also be diazotised further without being isolated.

The further diazotisation of the aminoazo dyestuffs (XI) with Z = H can be carried out, for example, in an acid, aqueous dispersion by means of sodium nitrite solution; for this purpose, the diazotisation temperatures can be between 0° and 30° C. Aminoazo dyestuffs of the formula (XI) with Z = H can furthermore also be diazotised indirectly by dissolving them in alkaline solutions, adding sodium nitrite solution and pouring the mixture into aqueous hydrochloric acid, or adding hydrochloric acid to the mixture.

The coupling of the diazotised aminoazo dyestuffs (XI) with the end components (XII) to give the disazo dyestuffs (XIII) is also carried out in the usual manner, preferably in an aqueous alkaline medium. The disazo dyestuffs of the formula (XIII) can be isolated by simply filtering them off, if necessary after addition of sodium chloride. If the dyestuffs are obtained in an impure form, they can be recrystallised in a known manner from hot water, if necessary with addition of alkali.

The reaction of the disazo dyestuffs (XIII) with the alkylene oxides to give the dyestuffs (I) is carried out in the usual manner, for example in an aqueous alkaline medium.

The reaction is most advantageously carried out at temperatures of 70°-90° C, if appropriate in an autoclave in the case of low-boiling alkylene oxides (for example propylene oxide). The most advantageous yields of alkylated product are obtained by introducing 2 to 4 mols of alkylene oxide into the reaction mixture per mol of phenolic dyestuff.

The more sparingly soluble dyestuffs (I) can be rendered readily water-soluble by mixing them with salts of strong bases and weak acids, for example trisodium phosphate, disodium hydrogen phosphate, sodium tetraborate, sodium metaphosphate, sodium metasilicate or sodium carbonate.

The new dyestuffs of the formula (I) can be isolated in the form of the free acid or as alkali metal salts or ammonium salts, or can be in this form, or can be employed in this form for their further use. Suitable alkali metal salts, in which the hydrogen atom of the --NH-- group is thus replaced by an alkali metal cation, are, for example, the sodium, potassium or lithium salts.

The new dyestuffs are particularly suitable for dyeing and printing natural and synthetic fibre materials containing amide groups, for example fibre materials of wool, silk and polyamide, such as poly-ε-caprolactam or the reaction product of hexamethylenediamine with adipic acid. The dyeings obtained, especially those on polyamide materials, are distinguished by good fastness properties, especially by good wet fastness properties and good light fastness properties. The neutral affinity, and the behaviour when combined with other suitable dyestuffs for such material, are also good. The dyestuffs of the formula (I) are employed for dyeing either in the form of the free acid (> NH) or as an alkali metal salt or as the ammonium salt. Because of their excellent solubility the dyestuffs are particularly suitable for the preparation of concentrated aqueous solutions.

In the examples which follow, parts denote parts by weight and percentages denote percentages by weight.

EXAMPLE 1

31.2 parts of (3-amino-benzenesulphonyl)-benzenesulphonamide are dissolved in 200 parts of water by addition of 10% strength sodium hydroxide solution, and 7.0 parts of sodium nitrite are added. The solution thus obtained is allowed to run into 200 parts of ice/H₂ O and 35 parts of concentrated hydrochloric acid and the diazotisation is carried out in 0.5 hour at 0°-5° C; the excess nitrous acid is then removed with amidosulphonic acid, the diazonium salt suspension is allowed to run into a solution of 20.5 parts of anilino-methanesulphonic acid and 9 parts of sodium bicarbonate in 100 parts of water at 0°-5° C and the pH is kept at between 5 and 7 by further addition of sodium bicarbonate. After completion of coupling, the product is salted out with sodium chloride, filtered off and washed with saturated sodium chloride solution. The moist dyestuff paste is stirred in 200 parts of 7% strength sodium hydroxide solution for 1 hour at 80°-90° C. After completion of the splitting off of the sulphomethyl group, the dyestuff is precipitated by adding sodium chloride, filtered off and washed with saturated sodium chloride solution.

The aminoazo dyestuff thus obtained is dissolved in 500 parts of water, 7.0 parts of sodium nitrite are added, the dyestuff is diazotised in 30 minutes at 10°-20° C by pouring the mixture into 1,000 parts of water and 30 parts of concentrated hydrochloric acid, and the excess nitrous acid is then destroyed with amidosulphonic acid. The diazonium salt suspension thus obtained is stirred into a solution of 9.5 parts of phenol and 4 parts of sodium hydroxide in 200 parts of water at 10°-20° C and the pH is kept at between 8 and 9 by adding 10% strength sodium hydroxide solution. After completion of coupling, the disazo dyestuff is filtered off and dissolved in 500 ml of water and 200 ml isopropanol and the pH is adjusted to 7.5-8.0, and 18 g of 1,2-butylene oxide are added dropwise at 70° C. The mixture is stirred for 10 hours at 70° C and allowed to cool, and the dyestuff which has precipitated is filtered off, washed with sodium chloride solution and dried in vacuo at 50° C. In the form of the free acid, the dyestuff corresponds to the formula ##STR25## It dyes polyamide, from a weakly acid or neutral bath, in yellow shades of good fastness properties.

If the procedure indicated in the preceding example is followed and the starting components, middle components, end components and alkylene oxides indicated in the table which follows are used, further disazo dyestuffs of the general formula (I) are obtained, which dye polyamide in yellow to bluish red shades.

                                      Table                                        __________________________________________________________________________     Example Starting component                                                                             Middle component                                                                             End component                                                                              Alkylene                     __________________________________________________________________________                                                       oxide                        2       (3-Amino-benzenesulphonyl)-                                                                    Aniline       o-Cresol    Propylene oxide                      benzenesulphonamide                                                    3       "               "             m-Cresol    "                            4       "               "             p-Cresol    "                            5       "               "             3-Methoxyphenol                                                                            "                            6       "               "             1-Hydroxy-2-ethyl-                                                                         "                                                                  benzene                                  7       "               "             2-Hydroxy-1,3-                                                                             1,2-Butylene oxide                                                 dimethyl-benzene                         8       "               "             2-Hydroxy-1,4-                                                                             "                                                                  dimethyl-benzene                         9       "               3-Amino-toluene                                                                              Phenol      "                            10      "               "             o-Cresol    "                            11      "               "             p-Cresol    "                            12      "               "             1-Hydroxy-4-ethyl-                                                                         "                                                                  benzene     "                            13      "               "             1-Hydroxy-3-ethoxy-                                                                        "                                                                  benzene                                  14      "               "             4-Hydroxy-1,2-                                                                             "                                                                  dimethyl-benzene                         15      "               3-Amino-4-methoxy-                                                                           Phenol      Propylene oxide                                      toluene                                                16      "               "             o-Cresol    2,3-Butylene oxide           17      "               "             4-tert.-Butylphenol                                                                        1,2-Butylene oxide           18      "               "             m-Cresol    "                            19      "               "             3-Methoxyphenol                                                                            "                            20      "               "             3-Ethoxyphenol                                                                             "                            21      "               "             2-Hydroxy-1,4-                                                                             "                                                                  dimethylbenzene                          22      "               "             3-Hydroxy-1,2-                                                                             "                                                                  dimethylbenzene                          23      "               "             p-Cresol    "                            24      "               3-Amino-anisole                                                                              Phenol      "                            25      "               "             o-Cresol    "                            26      "               "             p-Cresol    "                            27      "               "             m-Cresol    "                            28      "               "             4-tert.-Butylphenol                                                                        "                            29      "               "             3-Methoxyphenol                                                                            "                            30      "               "             2-Methoxyphenol                                                                            "                            31      "               "             2-Hydroxy-1,4-                                                                             Propylene oxide                                                    dimethylbenzene                          32      "               2-Aminotoluene                                                                               Phenol      1,2-Butylene oxide           33      "               "             o-Cresol    "                            34      "               "             p-Cresol    "                            35      "               "             4-Ethylphenol                                                                              "                            36      "               "             4-Hydroxy-1,2-                                                                             "                                                                  dimethylbenzene                          37      "               "             3-Methoxyphenol                                                                            "                            38      "               "             3-Ethoxyphenol                                                                             2,3-Butylene oxide           39      "               "             2-Isopropylphenol                                                                          "                            40      "               "             2-Hydroxy-1,3-                                                                             "                                                                  diethylbenzene                           41      "               3-Amino-ethyl-benzene                                                                        Phenol      "                            42      "               "             o-Cresol    Propylene oxide              43      "               "             p-Cresol    "                            44      "               "             4-Hydroxy-1,2-                                                                             1,2-Butylene oxide                                                 dimethylbenzene                          45      "               "             3-Methoxyphenol                                                                            "                            46      "               "             4-tert.-Butylphenol                                                                        "                            47      "               2-Amino-ethyl-benzene                                                                        Phenol      "                            48      "               "             p-Cresol    "                            49      "               "             o-Cresol    "                            50      "               "             4-Ethylphenol                                                                              "                            51      "               " 2-Methoxyphenol                                                                            "                                        52      "               2-Amino-anisole                                                                              Phenol      "                            53      "               "             o-Cresol    "                            54      "               "             p-Cresol    "                            55      "               "             3-Methoxyphenol                                                                            "                            56      "               "             4-Butoxyphenol                                                                             "                            57      "               "             2-Isopropylphenol                                                                          "                            58      "               3-Bromo-aniline                                                                              Phenol      "                            59      "               "             m-Cresol    "                            60      "               "             4-Ethylphenol                                                                              "                            61      "               "             2-Hydroxy-1,4-                                                                             "                                                                  dimethylbenzene                          62      "               3-Amino-ethoxy-benzene                                                                       Phenol      Propylene oxide              63      "               "             o-Cresol    Styrene oxide                64      "               "             4-tert.-Butylphenol                                                                        Propylene oxide              65      "               "             3-Methoxyphenol                                                                            "                            66      "               "             2-Methoxyphenol                                                                            "                            67      "               3-Chloro-aniline                                                                             Phenol      "                            68      "               "             p-Cresol    "                            69      "               "             2-secondary Butyl-                                                                         Glycidol                                                           phenyl                                   70      "               "             4-Ethylphenol                                                                              1,2-Butylene oxide           71      "               1-Amino-2,3-dimethyl-                                                                        Phenol      "                                                    benzene                                                72      "               "             m-Cresol    "                            73      "               "             p-Cresol    "                            74      "               "             4-Ethylphenol                                                                              "                            75      "               "             3-Hydroxy-1,2-                                                                             "                                                                  dimethylbenzene                          76      "               2-Amino-4-methoxy-                                                                           Phenol      "                                                    toluene                                                77      "               "             o-Cresol    Glycidyl methyl ether        78      "               "             4-tert.-Butylphenol                                                                        1,2-Butylene oxide           79      "               "             3-Methoxyphenol                                                                            "                            80      "               2-Amino-1,4-methoxy-                                                                         Phenol      "                                                    benzene                                                81      "               2-Amino-1,4-dimethoxy-                                                                       o-Cresol    "                                                    benzene                                                82      "               "             p-Cresol    "                            83      "               "             4-Ethylphenol                                                                              "                            84      "               "             4-Hydroxy-1,2-                                                                             "                                                                  dimethylbenzene                          85      "               1-Amino-2,5-dimethyl-                                                                        Phenol      "                                                    benzene                                                86      "               "             m-Cresol    Propylene oxide              87      "               "             4-Ethylphenol                                                                              "                            88      "               "             3-Methoxyphenol                                                                            "                            89      "               "             2-Hydroxy-1,4-                                                                             "                                                                  dimethylphenol                           90      "               2-Amino-4-ethoxy-                                                                            Phenol      "                                                    toluene                                                91      "               "             m-Cresol    2,3-Butylene oxide           92      "               "             p-Cresol    Glycidol                     93      "               "             3-Ethoxyphenol                                                                             "                            94      "               "             2-Ethylphenol                                                                              "                            95      "               2-Amino-1,4-diethoxy-                                                                        Phenol      Styrene oxide                                        benzene                                                96      "               "             4-Ethylphenol                                                                              1,2-Butylene oxide           97      "               "             4-tert.-Butylphenol                                                                        "                            98      "               α-Naphthylamine                                                                        p-Cresol    "                            99      "               "             o-Cresol    "                            100     "               "             Phenol      "                            101     "               "             3-Methoxyphenol                                                                            "                            102     "               "             4-Ethylphenol                                                                              "                            103     "               "             4-tert.-Butylphenol                                                                        "                            104     "               "             2-Hydroxy-1,4-                                                                             "                                                                  dimethylbenzene                          105     "               "             2-Hydroxy-1,3-                                                                             "                                                                  diethylbenzene                           106     "               5,6,7,8-Tetrahydro-                                                                          Phenol      "                                                    1-naphthylamine                                        107     "               "             o-Cresol    "                            108     "               "             p-Cresol    "                            109     "               "             4-Ethylphenol                                                                              "                            110     "               "             3-Methoxyphenol                                                                            "                            111     "               2-Methoxyaniline                                                                             m-Cresol    Propylene oxide              112     "               2,5-Dimethoxyaniline                                                                         Phenol      1,2-Butylene oxide           113     "               Aniline       m-Cresol    Styrene oxide                114     "               "             o-Cresol    Propylene oxide              115     (3-Amino-benzenesulphonyl)-                                                                    3-Methylaniline                                                                              Phenol      "                                    p-toluenesulphonamide                                                  116     "               "             m-Cresol    Glycidol                     117     (3-Amino-benzenesulphonyl)-                                                                    Aniline       o-Cresol    Glycidyl butyl ether                 o-toluenesulphonamide                                                  118     "               3-Methylaniline                                                                              o-Cresol    Glycidyl benzyl ether        119     (3-Amino-benzenesulphonyl)-                                                                    2,5-Dimethoxyaniline                                                                         o-Cresol    Propylene oxide                      butanesulphonamide                                                     120     (3-Amino-6-methyl-benzene-                                                                     2,5-Dimethoxyaniline                                                                         Phenol      Propylene oxide                      sulphonyl)-benzenesulphon-                                                     amide                                                                  121     (3-Amino-4-methyl-benzene-                                                                     Aniline       Phenol      Glycidyl acetate                     sulphonyl)-p-toluene-                                                          sulphonamide                                                           122     "               2,5-Dimethoxyaniline                                                                         m-Cresol    Propylene oxide              123     (3-Amino-4-methoxy-benzene-                                                                    "             Phenol      "                                    sulphonyl)-p-toluene-                                                          sulphonamide                                                           124     (2-Aminobenzenesulphonyl)-                                                                     "             o-Cresol    "                                    o-toluenesulphonamide                                                  125     (3-Amino-6-ethyl-benzene-                                                                      2-Methoxyaniline                                                                             o-Cresol    "                                    sulphonyl)-methane-                                                            sulphonamide                                                           126     "               3-Methylaniline                                                                              o-Cresol    1,2-Butylene oxide           127     (4-Amino-benzenesulphonyl)-                                                                    "             m-Cresol    "                                    p-toluenesulphonamide                                                  128     (4-Amino-benzenesulphonyl)-                                                                    Aniline       m-Cresol    Propylene oxide                      butanesulphonamide                                                     129     (3-Amino-4-chloro-5-methyl-                                                                    "             Phenol      "                                    benzenesulphonyl)-benzene-                                                     sulphonamide                                                           130     (4-Amino-5-methyl-benzene-                                                                     "             Phenol      "                                    sulphonyl)-methane-                                                            sulphonamide                                                           131     (3-Amino-benzenesulphonyl)-                                                                    "             m-Cresol    Isobutylene oxide                    benzenesulphonamide                                                    132     "               2-Amino-anisole                                                                              Phenol      "                            __________________________________________________________________________

DYEING EXAMPLE

0.1 g of the dyestuff of example 1 dissolved in 100 ml of hot water, 5 ml of 10% strength ammonium acetate solution are added and the mixture is diluted to a volume of 500 ml with water. 10 g of polyamide fibre are introduced into the dyebath, which is brought to the boil over the course of 20 minutes, 4 ml of 10% strength acetic acid are added and the mixture is kept at the boil for 1 hour. The material is then rinsed and dried at 70°-80° C. 

We claim:
 1. Disazo dyestuff which in the form of the free acid corresponds to the formula ##STR26## wherein B is 5,6,7,8-tetrahydro-1,4-naphthylene, 1,4-naphthylene, or 1-4 phenylene;R₁ is phenyl; phenyl substituted by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, nitrile, or nitro; C₁ -C₄ -alkyl; R₂ is chlorine, bromine, or alkyl or alkoxy having 1-4 carbon atoms; R₃ and R₄ independently of one another are hydrogen, chlorine, bromine, or alkoxy or alkyl having 1-4 carbon atoms; R₅ and R₆ independently of one another are hydrogen, alkyl having 1-4 carbon atoms, or alkoxy having 1-4 carbon atoms; R₇ represents ##STR27## R₈ and R₁₀ independently of one another are hydrogen or methyl; R₉ is methyl, ethyl, phenyl, hydroxymethyl, C₁ -C₄ -alkoxymethyl, benzyloxymethyl, C₁ -C₄ -alkyl-carbonyloxymethyl or C₂ -C₄ -alkenylcarbonyloxymethyl; the radical OR₇ is in the o- or p-position relative to the azo bridge, and m is a number from 0 to
 2. 2. Disazo dyestuff which in the form of the free acid corresponds to the formula ##STR28## wherein R₁ ' is phenyl; phenyl substituted with C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, nitrile, or nitro; or C₁ -C₄ -alkyl;R₂ is chlorine, bromine, or alkyl or alkoxy having 1-4 carbon atoms; R₃ and R₄ independently of one another are hydrogen, chlorine, bromine, or alkoxy or alkyl having 1-4 carbon atoms; R₅ and R₆ are hydrogen, alkyl with 1-4 carbon atoms, or alkoxy with 1-4 carbon atoms; R₇ represents ##STR29## R₈ and R₁₀ independently of one another are hydrogen or methyl; R₉ is methyl, ethyl, phenyl, hydroxymethyl, C₁ -C₄ -alkoxymethyl, benzyloxymethyl, C₁ -C₄ -alkyl-carbonyloxymethyl or C₂ -C₄ -alkenylcarbonyloxymethyl; the radical OR₇ is in the o- or p-position relative to the azo group; and m is a number from 0 to
 2. 3. Disazo dyestuff which in the form of the free acid corresponds to the formula ##STR30## wherein R₁ ' is phenyl; phenyl substituted with C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, nitrile, or nitro; or C₁ -C₄ -alkyl;R₂ ' is hydrogen, chlorine, bromine, methoxy, ethoxy, methyl, ethyl or trifluoromethyl; R₃ ' is hydrogen, chlorine, methyl, methoxy, ethyl, or ethoxy; R₄ ' is hydrogen, methyl, methoxy, ethyl, or ethoxy; R₅ ' and R₆ ' independently of one another are hydrogen, alkyl with 1-4 carbon atoms, or alkoxy with 1-4 carbon atoms; R₇ ' is 2-hydroxypropyl or 2-hydroxybutyl; and wherein the radical OR₇ ' is in the o- or p-position relative to the azo group.
 4. Disazo dyestuff which in the form of the free acid corresponds to the formula ##STR31## wherein R₁ " is phenyl, or methylphenyl;R₂ " is hydrogen, chlorine, bromine, methoxy, ethoxy, methyl, ethyl, or trifluoromethyl; R₃ " is hydrogen, chlorine, methyl, methoxy, ethyl, or ethoxy; R₄ " is hydrogen, methyl, methoxy, ethyl, or ethoxy; R₅ " and R₆ " independently of one another are hydrogen, alkyl with 1-4 carbon atoms, or alkoxy with 1-4 carbon atoms; R₇ ' is 2-hydroxypropyl or 2-hydroxybutyl; and the radical OR₇ ' is in o- or p-position relative to the azo group.
 5. Disazo dyestuff which in the form of the free acid corresponds to the formula ##STR32## wherein B' is 1,4-naphthylene or 5,6,7,8-tetrahydro-1,4-naphthylene;R₁ ' is phenyl; phenyl substituted with C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, nitrile, or nitro; or C₁ -C₄ -alkyl; R₂ is chlorine, bromine, or alkoxy or alkyl having 1-4 carbon atoms; R₅ and R₆ independently of one another represent hydrogen, alkyl with 1-4 carbon atoms, or alkoxy with 1-4 carbon atoms; R₇ represents ##STR33## R₈ and R₁₀ independently of one another are hydrogen or methyl; R₉ is methyl, ethyl, phenyl, hydroxymethyl, C₁ -C₄ -alkoxymethyl, benzyloxymethyl, C₁ -C₄ -alkyl-carbonyloxymethyl or C₂ -C₄ -alkenylcarbonyloxymethyl; the radical OR₇ is in the o- or p-position relative to the azo group, and m is a number from 0 to
 2. 6. Disazo dyestuff which in the form of the free acid corresponds to the formula ##STR34## wherein B' is 1,4-naphthylene radical or 5,6,7,8-tetrahydro-1,4-naphthylene;R₁ ' is phenyl; phenyl substituted with C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, halogen, nitrile, or nitro; or C₁ -C₄ -alkyl; R₂ ' is hydrogen, chlorine, bromine, methoxy, ethoxy, methyl, ethyl, or trifluoromethyl; R₅ ' and R₆ ' independently of one another are hydrogen, alkyl with 1-4 carbon atoms, or alkoxy with 1-4 carbon atoms; R₇ ' is 2-hydroxypropyl or 2-hydroxybutyl; and the radical OR₇ ' is in o- or p-position relative to the azo group.
 7. Dyestuff of claim 1 of the formula ##STR35##
 8. Dyestuff of claim 1 of the formula ##STR36##
 9. Dyestuff of claim 1 of the formula ##STR37##
 10. Dyestuff of claim 1 of the formula ##STR38##
 11. Dyestuff of claim 1 of the formula ##STR39## 